Are We Getting Too Soft?

I've been having the same conversation with different successful entrepreneurs lately. Whether they're Gen X, Boomers, or other Millennials, we keep circling back to the same challenge: finding people who see obstacles as puzzles to solve rather than walls that block progress.

What surprises me most is how universal this frustration seems to be. I’ve heard it from all types of successful, self-made people. A Baby Boomer entrepreneur running a large hospitality business, a successful PE fund manager, successful startup founders, etc... all describing the same pattern. And is almost without exception the biggest challenge successful people talk about. Smart people, good credentials, strong interviews. But when the work gets messy and the path gets unclear, something breaks down. The creative problem solving we need just isn't there.

One entrepreneur wondered if we're seeing a generational shift. "Maybe growing up during prosperous times with lots of safety nets creates a different relationship with struggle," he suggested. "When everyone gets a trophy and you're told to follow your dreams, maybe adversity becomes something to avoid rather than something that shapes you."

Another pushed back on this theory. She pointed out that every generation complains about the next one being soft. But then she paused and added something to the effect of: “Though I do notice my younger employees expect problems to have clean solutions. When they don't, there's this sense of betrayal, like the universe isn't playing fair."

So I got curious and looked at the research. What I found was really interesting. A report from Wake Forest found that in 1958, 92% of Americans agreed that "hardships build character." By the time we get to Gen Z, that number has dropped to 59%. Studies on grit and resilience show similar patterns, with younger cohorts scoring lower on measures of perseverance when facing obstacles.

The data suggests we might be witnessing a real shift in how people relate to adversity.

As I’ve been having these conversations, I’ve also had to confront my own bias. I spent a year homeless in high school, living in a work van with my dad. My family had been poor for generations going back to sharecroppers and mill workers. That background likely shaped how I see obstacles: as puzzles that need solving because giving up was never really an option. But I realized this lens might make me impatient with people who learned different lessons from their upbringing.

The question that keeps nagging at me is whether you can develop grit without experiencing real adversity. If you've always had the option to quit when things got too hard, how do you learn to push through when quitting would be easier? And more importantly, how do we build teams capable of tackling genuinely hard problems when so many people have been trained to expect smoother paths?

Building something exceptional requires dealing with exceptional challenges. There's no clean roadmap for creating something that hasn't existed before. The work is messy, the setbacks are real, and the solutions often require thinking that goes beyond what any school or previous job has taught you.

I wonder if the real divide isn't generational but attitudinal. Some people see comfort as the goal and structure their lives to minimize friction. Others see growth as the goal and understand that growth requires discomfort. The first group might be happier on average, but the second group builds the things that move the world forward.

Can you shift from the first mindset to the second? I've seen it happen, but it seems to require a conscious choice to seek out challenges rather than avoid them. To choose the harder path specifically because it's harder. To view setbacks as data rather than defeats.

Maybe that's what we should really be screening for: not past adversity, but present appetite for challenge and discomfort. Not what life has thrown at you, but what you've chosen to take on when easier options existed.

The entrepreneurs I spoke with are all still searching for answers. But we agreed on one thing: in a world that increasingly optimizes for comfort and efficiency, the ability to embrace productive discomfort might be the scarcest resource of all.